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Huber R., Marcourt L., Héritier M., Luscher A., Guebey L., Schnée S., Michellod E., Guerrier S., Wolfender J-L., Scapozza L., Köhler T., Gindro K., Queiroz E. F.

Generation of potent antibacterial compounds through enzymatic and chemical modifications of the trans-delta-viniferin scafold.

Scientific Reports, 13, (15986), 2023, 1-21.

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Zusammenfassung:

Stilbene dimers are well-known for their diverse biological activities. In particular, previous studies have demonstrated the high antibacterial potential of a series of trans-δ-viniferin-related compounds against gram-positive bacteria such as Staphylococcus aureus. The trans-δ-viniferin scaffold has multiple chemical functions and can therefore be modified in various ways to generate derivatives. Here we report the synthesis of 40 derivatives obtained by light isomerization, O-methylation, halogenation and dimerization of other stilbene monomers. The antibacterial activities of all generated trans-δ-viniferin derivatives were evaluated against S. aureus and information on their structure–activity relationships (SAR) was obtained using a linear regression model. Our results show how several parameters, such as the O-methylation pattern and the presence of halogen atoms at specific positions, can determine the antibacterial activity. Taken together, these results can serve as a starting point for further SAR investigations.

ISSN Print: 2045-2322
Digital Object Identifier (DOI): https://doi.org/10.1038/s41598-023-43000-5
Publikations-ID (Webcode): 54099 Per E-Mail versenden

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Generation of potent antibacterial compounds through enzymatic and chemical modifications of the trans-delta-viniferin scafold.

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Generation of potent antibacterial compounds through enzymatic and chemical modifications of the trans-delta-viniferin scafold.